NPASS Compound

Natural Product: NPC477319

Natural Product ID	NPC477319
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6,24-dimethyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-3-yl] octanoate
IUPAC Name	[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6,24-dimethyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-3-yl] octanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	118716652
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

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0 0 6.1996 0.7621 2.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 14 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 30 34 1 0 29 35 1 0 28 36 1 0 24 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 23 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 66 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 70 72 1 0 69 73 1 0 68 74 1 0 63 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 49 80 1 0 46 81 1 0 21 82 1 0 12 83 1 0 16 11 1 0 25 20 1 0 32 27 1 0 50 45 1 0 67 48 1 0 71 65 1 0 1 84 1 0 1 85 1 0 1 86 1 0 2 87 1 0 2 88 1 0 3 89 1 0 3 90 1 0 4 91 1 0 4 92 1 0 5 93 1 0 5 94 1 0 6 95 1 0 6 96 1 0 7 97 1 0 7 98 1 0 11 99 1 1 12100 1 6 14101 1 1 15102 1 6 16103 1 6 17104 1 0 18105 1 0 20106 1 1 21107 1 6 23108 1 1 24109 1 6 25110 1 6 27111 1 6 28112 1 1 29113 1 6 30114 1 6 31115 1 1 33116 1 0 33117 1 0 33118 1 0 34119 1 0 35120 1 0 36121 1 0 40122 1 6 41123 1 0 41124 1 0 41125 1 0 42126 1 0 42127 1 0 43128 1 0 43129 1 0 43130 1 0 45131 1 1 46132 1 6 48133 1 6 49134 1 6 50135 1 6 54136 1 0 54137 1 0 55138 1 0 55139 1 0 56140 1 0 56141 1 0 57142 1 0 57143 1 0 58144 1 0 58145 1 0 59146 1 0 59147 1 0 60148 1 0 60149 1 0 61150 1 0 61151 1 0 62152 1 0 62153 1 0 63154 1 1 65155 1 1 66156 1 6 68157 1 6 69158 1 1 70159 1 1 72160 1 0 72161 1 0 72162 1 0 73163 1 0 74164 1 0 75165 1 0 75166 1 0 76167 1 0 76168 1 0 77169 1 0 77170 1 0 78171 1 0 78172 1 0 79173 1 0 79174 1 0 79175 1 0 80176 1 0 81177 1 0 81178 1 0 81179 1 0 82180 1 0 82181 1 0 82182 1 0 83183 1 0 83184 1 0 83185 1 0 M END

Standard InCHIKey	MXBHWGIADFCCGD-HOBAKVMBSA-N
Standard InCHI	InChI=1S/C59H102O24/c1-10-13-15-19-24-28-37(60)77-47-33(7)73-56(45(68)43(47)66)80-49-35(9)75-59(53(79-54(70)30(4)12-3)52(49)83-55-44(67)41(64)39(62)31(5)71-55)81-48-34(8)74-57-46(69)50(48)78-38(61)29-25-21-18-16-17-20-23-27-36(26-22-14-11-2)76-58-51(82-57)42(65)40(63)32(6)72-58/h30-36,39-53,55-59,62-69H,10-29H2,1-9H3/t30-,31-,32+,33-,34-,35-,36-,39-,40-,41+,42-,43-,44+,45+,46+,47-,48-,49-,50-,51+,52+,53+,55-,56-,57-,58-,59-/m0/s1
SMILES	CCCCCCCC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@@H]1O)O)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)OC(=O)[C@@H](C)CC)O[C@H]4[C@@H](O[C@@H]5[C@@H]([C@@H]4OC(=O)CCCCCCCCC[C@@H](O[C@H]6[C@H](O5)[C@H]([C@H]([C@H](O6)C)O)O)CCCCC)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1194.68	Volume:	1180.737 ? Van der Waals volume.
Dense:	1.012	LogP:	3.968 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.897 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.032 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	Rigid Bonds:	49.0
TPSA:	333.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.938	Fsp³:	0.949
MCE-18:	125.217 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.543	Promiscuous compounds:	0.063

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.681	MDCK Permeability:	-5.037
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.024	30% Bioavailability (F30%):	0.188
50% Bioavailability (F50%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	90.301%	Volume Distribution (VD):	-0.129
Fu:	6.47% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.745
OATP1B3 inhibitor:	0.957	BCRP inhibitor:	0.0
BSEP inhibitor:	0.248

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.995 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.597

Half-life (T1/2):

2.785

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.16
Human Hepatotoxicity (H-HT):	0.398	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.713	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.736	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.748
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.263
BCF:	0.558 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.877 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.692 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.508 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Whole Plant	Dongshan, Nanjing, Jiangsu Province, China	2012-NOV	PMID[25314138]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38192648]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell line	4
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell line	U2OS	Homo sapiens	IC50	=	9400	nM	PMID[25314138]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	9500	nM	PMID[25314138]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	3700	nM	PMID[25314138]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	4100	nM	PMID[25314138]
NPT2	Others	Unspecified	n.a.	IC50	=	7700	nM	PMID[25314138]
NPT2	Others	Unspecified	n.a.	IC50	>	10000	nM	PMID[25314138]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC477319 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	23279
0.1-0.2	23421
0.2-0.3	2888
0.3-0.4	138
0.4-0.5	17
0.5-0.6	35
0.6-0.7	26
0.7-0.8	0
0.8-0.85	4
0.85-0.9	9
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC143421
0.961	High Similarity	NPC290012
0.9605	High Similarity	NPC307400
0.9605	High Similarity	NPC27289
0.9125	High Similarity	NPC123204
0.9	High Similarity	NPC126685
0.8933	High Similarity	NPC113745
0.8933	High Similarity	NPC477320
0.8933	High Similarity	NPC477323
0.8933	High Similarity	NPC477325
0.8933	High Similarity	NPC609436
0.8861	High Similarity	NPC472204
0.8846	High Similarity	NPC267592
0.8765	High Similarity	NPC183888
0.8765	High Similarity	NPC259294
0.84	Intermediate Similarity	NPC146380
0.8171	Intermediate Similarity	NPC119583
0.8125	Intermediate Similarity	NPC477326
0.8072	Intermediate Similarity	NPC483170
0.7976	Intermediate Similarity	NPC115013
0.7875	Intermediate Similarity	NPC604005
0.7875	Intermediate Similarity	NPC605014
0.7778	Intermediate Similarity	NPC89843
0.7609	Intermediate Similarity	NPC63404
0.7561	Intermediate Similarity	NPC478734
0.7558	Intermediate Similarity	NPC477317
0.7558	Intermediate Similarity	NPC477318
0.7531	Intermediate Similarity	NPC22742
0.7531	Intermediate Similarity	NPC477346
0.75	Intermediate Similarity	NPC281563
0.7471	Intermediate Similarity	NPC184915
0.7471	Intermediate Similarity	NPC224953
0.7419	Intermediate Similarity	NPC35338
0.7419	Intermediate Similarity	NPC204214
0.7419	Intermediate Similarity	NPC92283
0.7381	Intermediate Similarity	NPC478733
0.7356	Intermediate Similarity	NPC169345
0.7303	Intermediate Similarity	NPC44782
0.7294	Intermediate Similarity	NPC146992
0.7294	Intermediate Similarity	NPC85759
0.7292	Intermediate Similarity	NPC10121
0.7292	Intermediate Similarity	NPC198918
0.7262	Intermediate Similarity	NPC477344
0.7209	Intermediate Similarity	NPC297768
0.7209	Intermediate Similarity	NPC472205
0.7126	Intermediate Similarity	NPC294748
0.7089	Intermediate Similarity	NPC606819
0.7059	Intermediate Similarity	NPC600446
0.7059	Intermediate Similarity	NPC605013
0.7045	Intermediate Similarity	NPC238264
0.7045	Intermediate Similarity	NPC476087
0.7045	Intermediate Similarity	NPC475667
0.7045	Intermediate Similarity	NPC477345
0.7011	Intermediate Similarity	NPC173328
0.6966	Remote Similarity	NPC238056
0.6966	Remote Similarity	NPC478732
0.6947	Remote Similarity	NPC124878
0.6947	Remote Similarity	NPC231888
0.6889	Remote Similarity	NPC475270
0.6889	Remote Similarity	NPC475327
0.686	Remote Similarity	NPC158302
0.6782	Remote Similarity	NPC109887
0.6742	Remote Similarity	NPC186992
0.6667	Remote Similarity	NPC475164
0.663	Remote Similarity	NPC472200
0.66	Remote Similarity	NPC10883
0.6506	Remote Similarity	NPC477350
0.6458	Remote Similarity	NPC475241
0.6421	Remote Similarity	NPC473605
0.6421	Remote Similarity	NPC475375
0.6381	Remote Similarity	NPC472352
0.6374	Remote Similarity	NPC478730
0.6211	Remote Similarity	NPC269318
0.618	Remote Similarity	NPC477331
0.6161	Remote Similarity	NPC147032
0.6136	Remote Similarity	NPC477349
0.6105	Remote Similarity	NPC475525
0.6105	Remote Similarity	NPC475540
0.6064	Remote Similarity	NPC478731
0.6042	Remote Similarity	NPC476066
0.5938	Remote Similarity	NPC163409
0.5818	Remote Similarity	NPC471024
0.581	Remote Similarity	NPC290276
0.581	Remote Similarity	NPC611287
0.5794	Remote Similarity	NPC600721
0.5794	Remote Similarity	NPC605872
0.573	Remote Similarity	NPC477329
0.5698	Remote Similarity	NPC478729
0.5688	Remote Similarity	NPC600940
0.5673	Remote Similarity	NPC77651
0.5638	Remote Similarity	NPC479061
0.5625	Remote Similarity	NPC478726
0.5618	Remote Similarity	NPC477330
0.5607	Remote Similarity	NPC600672
0.5591	Remote Similarity	NPC479059
0.5579	Remote Similarity	NPC479060
0.5524	Remote Similarity	NPC28069
0.5484	Remote Similarity	NPC477332
0.5474	Remote Similarity	NPC60849
0.5463	Remote Similarity	NPC610996
0.5444	Remote Similarity	NPC477328
0.5417	Remote Similarity	NPC479058
0.5413	Remote Similarity	NPC471025
0.5408	Remote Similarity	NPC162925
0.5347	Remote Similarity	NPC478728
0.5294	Remote Similarity	NPC478727
0.5268	Remote Similarity	NPC610997
0.5258	Remote Similarity	NPC44682
0.5258	Remote Similarity	NPC478724
0.5165	Remote Similarity	NPC475425
0.5155	Remote Similarity	NPC478722
0.5155	Remote Similarity	NPC478725
0.5102	Remote Similarity	NPC478723
0.5056	Remote Similarity	NPC169085
0.505	Remote Similarity	NPC479057

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC477319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7463
0.1-0.2	1619
0.2-0.3	67
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data